Benzyl Alcohol → Dibenzyl 2-hydroxybutanedioate

Participants

Reaction Conditions

Reaction Steps

Dibenzyl-DL-malate was prepared using the method of Lee et al, J. Chem. Soc. Perkin Trans. I, 1995, 2877. To a three-neck 1 L round-bottomed flask equipped with a reflux condenser, Dean-Stark trap, thermocouple and mechanical stirrer, were added DL-malic acid (81.96 g), benzyl alcohol (132.0 g), toluene (620 mL) and p-toluenesulfonic acid (1.165 g). The mixture was placed under nitrogen and heated to reflux. At 100° C., two phases started to collect in the Dean-Stark trap. After 2 hr, the reaction temperature was increased to 105° C. for 1.5 hr. The crude product was neutralized with saturated sodium bicarbonate and poured into a separatory funnel. The organic layer was washed with saturated sodium bicarbonate twice, washed once with water, and dried over magnesium sulfate. The toluene was removed via rotary evaporation. Two-thirds of the crude product were purified via column chromatography (20% ethyl acetate in hexane eluent). Residual benzyl alcohol was removed via vacuum distillation to give a low viscosity, clear, colorless oil with no detectable odor (49.9 g, 28% yield).

Provenance & Evidence